Chemistry:Dihydrotestosterone undecanoate
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| Other names | DHTU; 5α-Dihydrotestosterone 17β-undecanoate; Androstanolone undecanoate; Stanolone undecanoate; 5α-Androstan-17β-ol-3-one 17β-undecanoate; 3-Oxo-5α-androstan-17β-yl undecanoate |
| Routes of administration | By mouth[1] |
| Drug class | Androgen; Anabolic steroid; Androgen ester |
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| Formula | C30H50O3 |
| Molar mass | 458.727 g·mol−1 |
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Dihydrotestosterone undecanoate (DHTU), also known as androstanolone undecanoate or stanolone undecanoate, is a synthetic androgen and anabolic steroid (AAS) which was never marketed.[2][1][3][4] It is an androgen ester; specifically, it is the C17β undecanoate (undecylate) ester of dihydrotestosterone (DHT).[2][1][3][4][5] DHTU is a prodrug of DHT.[2][5][4] Similarly to testosterone undecanoate (TU), DHTU is orally active.[1][3][4] It occurs as an important active metabolite of oral TU.[6][2][5][7][8] The 5α-reductase inhibitor finasteride in combination with oral TU has no effect on the first-pass transformation of TU into DHTU or DHT, probably because of its unique lymphatic route of absorption.[9] Oral DHTU may be absorbed by the lymphatic system similarly to TU, and this may explain its oral bioavailability.[2][1][3][4]
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Prolactin secretion in the human male is increased by endogenous oestrogens and decreased by exogenous/endogenous androgens". International Journal of Andrology 7 (1): 53–60. February 1984. doi:10.1111/j.1365-2605.1984.tb00759.x. PMID 6715064.
- ↑ 2.0 2.1 2.2 2.3 2.4 "Dihydrotestosterone: Biochemistry, Physiology, and Clinical Implications of Elevated Blood Levels". Endocrine Reviews 38 (3): 220–254. June 2017. doi:10.1210/er.2016-1067. PMID 28472278.
- ↑ 3.0 3.1 3.2 3.3 "Androgens in the feedback regulation of gonadotropin secretion in men: effects of administration of dihydrotestosterone to eugonadal and agonadal subjects and of spironolactone to eugonadal subjects". Andrologia 16 (4): 289–298. 1984. doi:10.1111/j.1439-0272.1984.tb00286.x. PMID 6433746.
- ↑ 4.0 4.1 4.2 4.3 4.4 "Human male sexual functions do not require aromatization of testosterone: a study using tamoxifen, testolactone, and dihydrotestosterone". Archives of Sexual Behavior 14 (6): 539–548. December 1985. doi:10.1007/BF01541754. PMID 4084053.
- ↑ 5.0 5.1 5.2 "Importance of measuring testosterone in enzyme-inhibited plasma for oral testosterone undecanoate androgen replacement therapy clinical trials". Future Science OA 1 (4): FSO55. November 2015. doi:10.4155/fso.15.55. PMID 28031910.
- ↑ "Lymphatic Adsorption of Orally Administered Prodrugs". Prodrugs: Challenges and Rewards. Springer Science & Business Media. 26 August 2007. pp. 668–. ISBN 978-0-387-49785-3. https://books.google.com/books?id=Ld4scqFQmgYC&pg=PA668.
- ↑ "Testosterone undecanoate: a new orally active androgen". Acta Endocrinologica 80 (1): 179–187. September 1975. doi:10.1530/acta.0.0800179. PMID 1098350.
- ↑ "Lymphatic absorption and metabolism of orally administered testosterone undecanoate in man". Klinische Wochenschrift 54 (18): 875–879. September 1976. doi:10.1007/bf01483589. PMID 966635.
- ↑ "Steady-state pharmacokinetics of oral testosterone undecanoate with concomitant inhibition of 5α-reductase by finasteride". International Journal of Andrology 34 (6 Pt 1): 541–547. December 2011. doi:10.1111/j.1365-2605.2010.01120.x. PMID 20969601.
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